Pyridine → N-(6-bromo-5-chloropyridin-2-yl)benzamide

HRID 1521938Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1521938
[Br:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[Cl:9].N1C=CC=CC=1.[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>ClCCl>[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:5]=[CH:4][C:3]=1[Cl:9]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 534011936-Bromo-5-chloropyridin-2-amine

Produkt 1

HCID 90412314N-(6-bromo-5-chloropyridin-2-yl)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of Example 11A (400 mg, 1.928 mmol) in dichloromethane (20 mL) was added pyridine (0.468 mL, 5.78 mmol) followed by benzoyl chloride (0.325 g, 2.314 mmol) and the mixture was stirred for 2 hours. The mixture was concentrated and the residue was dissolved in ethyl acetate, washed with sodium bicarbonate solution, water and brine, and dried over anhydrous sodium sulfate. Filtration, concentration and purification by column chromatography (silica gel, 10% ethyl acetate in hexane) afforded the title compound. LCMS: 311 (M+H)+.

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with sodium bicarbonate solution, water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationFiltration, concentration and purification by column chromatography (silica gel, 10% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-17b5a27fd8c343f8ac24e8af0731ba07
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073922B2

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